9-(2,5-di-O-acetyl-β-D-glycero-pent-3-enofuranosyl)hypoxanthine | 174275-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(2,5-di-O-acetyl-β-D-glycero-pent-3-enofuranosyl)hypoxanthine
• 英文别名: [(2R,3R)-3-acetyloxy-2-(6-oxo-1H-purin-9-yl)-2,3-dihydrofuran-5-yl]methyl acetate
• CAS: 174275-88-8
• 化学式: C₁₄H₁₄N₄O₆
• 分子量: 334.288
• InChiKey: IUGAGXDOVNMRPK-QMTHXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(2,5-di-O-acetyl-β-D-glycero-pent-3-enofuranosyl)hypoxanthine 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 9-<2-O-acetyl-5-(tert-butyldiphenylsilyl)-β-D-glycero-pent-3-enofuranosyl>hypoxanthine
  参考文献：
  名称：

  Allylic Substitution of 3‘,4‘-Unsaturated Nucleosides:  Organosilicon-Based Stereoselective Access to 4‘-C-Branched 2‘,3‘-Didehydro-2‘,3‘-dideoxyribonucleosides

  摘要：

  Reactions of organosilicon reagents (such as allyltrimethylsilane, silyl enol ethers, cyanotrimethylsilane) with 3',4'-unsaturated nucleosides (of uracil, N-4-acetylcytosine, and hypoxanthine) having an allyl ester structure were investigated in the presence of a Lewis acid in CH2Cl2. In the cases of uracil and N-4-acetylcytosine derivatives, SnCl4 appeared to be suitable, whereas the use of EtAlCl(2) was necessary for the hypoxanthine derivatives. The main pathway of these reactions was found to be a-face-selective S(N)2' allylic substitution, irrespective of the configuration of 2'-0-acyl leaving group. As a result, a new stereoselective operation for C-C bonds formation leading to 4'-carbon-substituted 2',3'-didehydro-2',3'-dideoxyribonucleosides has been disclosed for the first time. Stereochemistry of these 4'-C-branched products can be assigned on the basis of H-1 NMR spectroscopy in terms of the anisotropic shift of H-5 of the pyrimidine base (or H-8 of the hypoxanthine), which is caused by the 5'-0-(tert-butyldiphenylsilyl) protecting group.

  DOI：

  10.1021/jo9516190
• 作为产物：
  描述：

  1-(2,5-di-O-acetyl-3-deoxy-3-iodo-β-D-xylofuranosyl)hypoxanthine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以95%的产率得到9-(2,5-di-O-acetyl-β-D-glycero-pent-3-enofuranosyl)hypoxanthine
  参考文献：
  名称：

  Allylic Substitution of 3‘,4‘-Unsaturated Nucleosides:  Organosilicon-Based Stereoselective Access to 4‘-C-Branched 2‘,3‘-Didehydro-2‘,3‘-dideoxyribonucleosides

  摘要：

  Reactions of organosilicon reagents (such as allyltrimethylsilane, silyl enol ethers, cyanotrimethylsilane) with 3',4'-unsaturated nucleosides (of uracil, N-4-acetylcytosine, and hypoxanthine) having an allyl ester structure were investigated in the presence of a Lewis acid in CH2Cl2. In the cases of uracil and N-4-acetylcytosine derivatives, SnCl4 appeared to be suitable, whereas the use of EtAlCl(2) was necessary for the hypoxanthine derivatives. The main pathway of these reactions was found to be a-face-selective S(N)2' allylic substitution, irrespective of the configuration of 2'-0-acyl leaving group. As a result, a new stereoselective operation for C-C bonds formation leading to 4'-carbon-substituted 2',3'-didehydro-2',3'-dideoxyribonucleosides has been disclosed for the first time. Stereochemistry of these 4'-C-branched products can be assigned on the basis of H-1 NMR spectroscopy in terms of the anisotropic shift of H-5 of the pyrimidine base (or H-8 of the hypoxanthine), which is caused by the 5'-0-(tert-butyldiphenylsilyl) protecting group.

  DOI：

  10.1021/jo9516190